If you’re looking for a place where you’ll feel completely transported back in time, this is it.
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The intimate lounge wouldn’t be slinging the delicious cocktails they are today without becoming the second place in the city to obtain a liquor license after Prohibition. Located in The Drake Hotel, a Chicago landmark, this place is the definition of old-time-y elegance. Coq d’Or Photo Credit: Chicago Bar Project Originally called El-Side Tavern for its location beneath CTA train tracks, Kelly’s Pub is a great spot to reminisce the history of Chicago. This bar is well-known by DePaul University students who frequent here on the weekends, and god knows also the weeknights. Kelly’s Pub Photo Credit: FlickrĪn Irish mainstay, Kelly’s is one of the oldest family-owned pubs in Chicago, opening just after Prohibition was repealed and the alcohol flowed freely again. And it’s still known for getting pretty rowdy now. So, as you can imagine, it was probably pretty rowdy back then. After the ban ended, it was in the group of the first Chicago establishments to receive a liquor license. Owned by the same family for three generations, it began as a totally innocent ( ahem) “soda shop” during the tail-end of the nation’s dry years. Named after the corner of Burling and Wrightwood where it stands, this Lincoln Park dive is beloved by the neighborhood. The Burwood Tap Photo Credit: Burwood Tap
And (of course) it operated for a while as a speakeasy. According to them, the building itself was formerly owned by Schlitz during the first World War. The impact this place has on Chicago history speaks for itself – just browse through their collection of memories submitted to their website by nostalgic patrons. When Frank Sinatra is one of your regulars, you know you’ve made history. Twin Anchors Restaurant & Tavern Photo Credit: Twin Anchors This place dishes out massive portions, so be sure to come with an appetite. Don’t be fooled by its somewhat nondescript appearance. Serving up traditional Chinese eats to hungry locals since the ’30s, this place has never left its spot in Irving Park. Orange Garden Photo Credit: Mark 2400 via Flickr Having been frequented by a variety of personalities and iconic names throughout its history, visiting here will make you feel apart of something larger than life. Discreetly located underneath the Canterbury Courts apartments, this is the place to go when you want to sing the night away. This piano bar in the Gold Coast proudly totes the third oldest liquor license in the city. Although it dates back to the ’20s, step inside this vibrantly decorated space and it’ll instantly feel timeless. This family business has worked for decades upon decades to provide top-notch, regional Italian eats, and has one of the most impressive collections of wine in the city to back it up. Treat yourself to not one – but three restaurants in a single, historic location.
Italian Village Photo Credit: Italian Village This breakfast diner is known throughout the world, having been visited by politicians, celebrities, and athletes alike, making it a staple among Chicago’s oldest restaurants. The level of hospitality provided at this place rivals none, and anyone who’s been there can attest! The second you walk in, you’ll feel like you’re dining with family, and it’s been that way for decades. Today, it has a modern speakeasy downstairs called The Drifter, where you can experience what it may have been like to come here in the ’20s.
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The name comes from its green door – a secret code that served as a beacon for anyone trying to get some of that giggle water. Green Door Tavern Photo Credit: Green Door Tavernīuilt shortly after the Fire, one of the city’s most well-known, long-standing establishments was one of the only wooden buildings left after a law was passed to prohibit them. An absolute staple in the Taylor Street area of Little Italy, it’s a true veteran of Chicago’s oldest restaurants, and the food will have you coming back for more, guaranteed. There’s something about Italian food that it just seems to taste better if it’s made with generations of family tradition behind it. Advertisement Pompei Photo Credit: Pompei